| 1.Research Institution | Tokyo Institute of Technology | |
| 2.Research Area | Integrated Fields | |
| 3.Research Field | Production of Novel Useful Substances through Integration of Life Sciences and Chemistry | |
| 4.Term of Project | FY1996〜FY2000 | |
| 5.Project Number | 96I00302 | |
| 6.Title of Project | Mechanistic Analysis and Engineering of Secondary Metabolism Directed toward the Designer Enzyme Systems |
| Name | Institution,Department | Title of Position |
| KAKINUMA, Katsumi | Tokyo Institute of Technology, Graduate School of Science and Engineering | Professor |
8.Core Members
| Names | Institution,Department | Title of Position |
| EBIZUKA, Yutaka | University of Tokyo, Graduate School of Pharmaceutical Sciences | Professor |
| SAITO, Kazuki | Chiba University, Faculty of Pharmaceutical Sciences | Professor |
| ASANO, Yasuhisa | Toyama Prefectural University, Faculty of Engineering | Professor |
9.Cooperating Researchers
| Names | Institution,Department | Title of Position |
| EGUCHI, Tadashi | Tokyo Institute of Technology, Graduate School of Science and Engineering | Assoc. Prof. |
| FUJII, Isao | University of Tokyo, Graduate School of Pharmaceutical Sciences | Assoc. Prof. |
| KATO, Yasuo | Toyama Prefectural University, Faculty of Engineering | Assoc. Prof. |
10.Summary of Research Results
|
Microbial and plant enzyme systems were studied to develop novel approaches for useful compounds. The biosynthetic gene clusters of 2-deoxystreptamine-containing antibiotics, vicenistatin antitumor antibiotic and benzoisochromanequinone antibiotics were identified and sequenced. The mechanisms of key biosynthetic reactions were elucidated on the genetic, enzymic, and molecular levels. Analysis of genetic constitution of a series of PKSes gave new insight into the pathways and enzymes of polyketide biosyntheses. A carbocycle-forming biosynthetic enzyme was overproduced and applied to a novel chemo-enzymatic synthesis of catechol from sustainable glucose resource. Fungal PKS systems were also analyzed and a new polyketide biosynthetic pathway was elucidated. The triterpene synthase genes were cloned from various plants and sequenced. Construction of point-mutants and chimera poly-peptides made significant finding that the product selectivity of these synthases was controlled by rather small variation of amino acid and even a single mutation could alter the product contents. Differential display analysis of Perilla variants and genetic analysis allowed identifying the anthocyanin glucosyl transferase gene of the biosynthesis of anthocyanin pigments and the same gene was further identified from other plants as well. Cloning and over-expression of the responsible genes and chemical analysis precisely determined the mechanism and regulation of anthocyanidine formation in plants. Plant flavonoid biosynthetic enzymes were studied by genome analysis and a specific regulator gene was identified. In the metabolism of amino acids and related products, the genes for key biosynthetic enzymes of plant β-substituted alanines and microbial opine dehydrogenase were genetically cloned and overproduced. The latter enzyme and its site-specific mutants were structurally studied by X-ray crystallography and the reaction mechanism was precisely elucidated. Microbial aldoxime-nitrile pathway was discovered and aldoxime dehydratase was purified from soil bacteria. The molecular cloning of the responsible gene further allowed its overproduction and application for the enzymatic preparation of nitriles. |
11.Key Words
(1)Enzyme Mechanism、(2)Molecular Analysis of Biosynthetic Genes、(3)Enzyme Engineering
(4)Engineered Biosynthesis、(5)Metabolic Control、(6)Antibiotics
(7)Amino Acid Metabolism、(8)Isoprenoids、(9)Alkaloids
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| M. Yamazaki | Molecular cloning and biochemical characterization of a novel anthocyanin 5-O-glucosyltransferase by mRNA differential display for plant formas regarding anthocyanin. | |||
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| K. Saito | Direct evidence for anthocyanidin synthase as a 2-oxoglutarate-dependent oxygenase: molecular cloning and functional expression of cDNA from a red forma of Perilla frutescens. | |||
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| Y. Hatzfeld | Identification of two putative nitrate transporters highly homologous to CHL1 from Arabidopsis thaliana (accession No. AJ011604 and AJ131464). | |||
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| Plant Physiol | 119 | 1999 | 805 | |
| Author | Title of Article | |||
| C. -L. Ho | Plastidic pathway of serine biosynthesis. Molecular cloning and expression of 3-phosphoserine phosphatase from Arabidopsis thaliana. | |||
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| Z. Gong | A light inducible Myb-like gene that is specifically expressed in red Perilla Frutescens and presumably acts as a determining factor of the anthocyanin forma. | |||
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| H. Takagi | Improved L-cysteine and L-cystine production by feedback inhibition-insensitive serine acetyltransferase from Arabidopsis thaliana in Escherichia coli. | |||
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| H. Takahashi | Cloning of an Arabidopsis cDNA encoding a chloroplast localizing sulfate transporter isoform. | |||
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| J. Exp. Botany | 340 | 1999 | 1713-1714 | |
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| Z. Gong | A constitutively expressed Myc-like gene involved in anthocyanin biosynthesis from Perilla Frutescens: Molecular characterization. heterologous expression in transgenic plants and transactivation in yeast cells. | |||
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| Plant Mol. Biol. | 41 | 1999 | 33-44 | |
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| H. Takahashi | Identification of two leaf-specific sulfate transporters in Arabidopsis thaliana | |||
| Journal | Volume | Year | Pages Concerned | |
| Plant Physiol | 121 | 1999 | 686 | |
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| K. Inoue | Determination of the sites required for the allosteric inhibition of serine acetyl-transferase by L-cysteine in plants. | |||
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| Eur. J. Biochem. | 260 | 1999 | 220-227 | |
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| T. Leustek | Sulfate transport and assimilation. | |||
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| Plant Physiol | 120 | 1999 | 637-643 | |
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| K. Saito | Regulation of sulfate transport and synthesis of sulfur-containing amino acids. | |||
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| Curr. Opin. Plant. Biol | 2000 | 188-195 | ||
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| Y. Hatzfeld | Evidence for the existence of rhodanese (thiosulfate:cyanide sulfurtransferase) in plants: preliminary chracterization of two rhodanese cDNAs from Arabidopsis thaliana. | |||
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| FEBS Lett. | 470 | 2000 | 147-150 | |
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| Y. Hatzfeld | β-Cyanoalanine synthase is a mitochondrial cysteine synthase-like protein in spinach and Arabidopsis thaliana. | |||
| Journal | Volume | Year | Pages Concerned | |
| Plant Physiol | 123 | 2000 | 1163-1171 | |
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| Y. Hatzfeld | Functional chracterization of a gene encoding a fourth ATP sulfurylase isoform from Arabidopsis thaliana. | |||
| Journal | Volume | Year | Pages Concerned | |
| Gene | 248 | 2000 | 51-58 | |
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| H. Takahashi | The roles of three functional sulfate transporters involved in uptake and translocation of sulfate in Arabidopsis thaliana. | |||
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| M. Y. Hirai | Biochemical and partial molecular characterization of bitter and sweet forms of Lupinus angustifolius, an experimental model for study of molecular regulation of qunolizidine alkaloid biosynthesis. | |||
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| Chem. Pharm. Bull | 48 | 2000 | 1458-1461 | |
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| Y. Urano | Molecular cloning and functional characterization of cDNAs encoding cysteine synthase and serine acetyltransferase that may be responsible for high cellular cysteine content in Allium tuberosum. | |||
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| Gene | 257 | 2000 | 269-277 | |
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| Z. -Z. Gong | Critical role of alanine-161 in Delila protein involved in regulation of anthocyanin pigmentation for transcriptional activation in yeast. | |||
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| Plant Biotechnology | 17 | 2000 | 331-335 | |
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| K. Saito | Feasible production of camptothecin by hairy root culture of Ophiorriza pumila. | |||
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| Plant Cell Rep (in press) | 2001 | |||
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| W. Shitthithaworn | Geranylgeranyl diphosphate synthase from Scoparia dulcis and Croton sublyratus. Plastid localization and conversion to a farnesyl diphosphate synthase by mutagenesis. | |||
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| Chem. Pharm. Bull. | 49 | 2001 | 197-202 | |
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| M. Noji | Cysteine synthase overexpression in Nicotiana tabacum confers tolerance to sulfurcontaining environmental pollutants. | |||
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| Plant Physiol (in press) | 2001 | |||
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| C. -L. Ho | Molecular biology of the plastidec phosphorylated serine biosynthetic pathway in Arabidopsis thaliana. | |||
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| Amino Acids (in press) | 2001 | |||
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| J. Nakajima | cDNA cloning and gene expression of anthocyanidin synthase from Torenia fournieri. | |||
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| Plant Biotechnology | 17 | 2000 | 331-335 | |
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| Y. Asano | Z-Phenylacetoaldoxime degradation by a novel aldoxime dehydratase from Bacillus sp. strain OxB-1 | |||
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| FEMS Micro | 158 | 1998 | 185-190 | |
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| K. L. Britton | The Crystal Structure of the N-(1-D-Carboxyethyl)-L-norvaline dehydrogenase from Arthrobacter sp. strain 1C. | |||
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| Arch Microbiol. | 170 | 1998 | 85-90 | |
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| K. L. Britton | Crystallization of Arthrobacter sp. Strain 1C opine dehydrogenase and its complex with NAD. | |||
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| Acta Cryst. D. | 5 | 1998 | 593-601 | |
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| Y. Kato | Nitrile hydratase involved in aldoxime metabolism from Rhodococcus sp. strain YH3-3 -purification and characterization- | |||
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| Eur. J. Biochem. | 263 | 1999 | 662-670 | |
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| Y. Kato | A new enzymatic method of nitrile synthesis by Rhodococcus sp.Strain YH3-3. | |||
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| J. Molec. Catal. B:Enzymatic | 6 | 1999 | 249-256 | |
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| Y. Kato | Opine dehydrogenase and secondary-amine dicarboxylic acids | |||
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| Encyclopedia of Bioprocess Technology: Fermentation, Biocatalysis, and Bioseparation M. C. Flickinger and S. W. Drew (ed). John Wiley & Sons. Inc., New York | 1999 | 1851-1858 | ||
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| Y. Kato | A novel heme-containing lyase, phenylacetaldoxime dehydratase from Bacillus sp. strain OxB-1: purification. characterization. and molecular cloning of the gene. | |||
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| Biochemistry | 39 | 2000 | 800-809 | |
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| Y. Kato | Distribution of aldoxime dehydratase in Microorganisms. | |||
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| Appl. Environ. Microbiol | 66 | 2000 | 2290-2296 | |
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| Y. Asano | Selecton and directed evolution of new microbial biocatalysts and their application to organic synthesis. | |||
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| Agric. Chem. Biotechnol. | 43 | 2000 | 207-210 | |
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| Y. Asano | Overview of screening for new microbial catalysts and their uses in organic synthesis Selection and optimization of biocatalysts- | |||
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| K. Kakinuma | Chirality Transfer on Carbohydrate Template: A Versatile Approach for Chiral Deuterium Labeling Svnthesis and Applications of Isotopically Labelled Compounds | |||
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| 1998 | 543-546 | |||
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| H. Hayashi | Molecular Cloning of Oxidosqualene Cyclase cDNA from Panax ginseng:The Isogene that Encodes β-Amyrin Synthase | |||
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| Elsevier Science B. V. Amsterdam | 1998 | 421-427 | ||
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| S. You | Biosynthetic Studies on Steroid Saponins, Towards Natural Medicine Research in the 21st Century. | |||
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| Elsevier Science B. V. Amsterdam | 1998 | 429-441 | ||